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If your cultural understanding of the city of Baltimore starts and ends with “The Wire,” may I present Jay Duplass’ “The Baltimorons.” Far from a crime-ridden hellhole, Baltimore is presented in the film as a lovely, moody place, a harbor town painted in dark blues and grays. We even get an elegiac shot of the Key Bridge before it collapsed in 2024.
It’s also Christmas Eve, although there isn’t a flake of snow on the ground. That might be too obvious for the understated emotions conjured up by writer-director Duplass and co-writer and star Michael Strassner (a Charm City native). Instead, “Baltimorons” angles to be another “Holdovers,” a Yuletide tale of two very different people forced together who find themselves unexpectedly bonding.
Strassner plays Cliff Cashin, a local comedian who was this close to getting a spot on a “Saturday Night Live”-type TV show but didn’t quite get there. He’s at his lowest point in the opening scene, an alcoholic who tries and fails to hang himself. It’s funnier than it sounds.
Six months later, Cliff is in recovery and associates his old comedy career with a lot of bad memories. Instead, he’s trying to make a go of a normal life, taking classes to become a mortgage broker, engaged to a nice girl (Olivia Luccardi).
I usually can’t stand to see anything Christmassy until after Thanksgiving, for “The Baltimorons” I’ll make an exception.
It’s a life that clearly doesn’t suit Cliff, and he knows it. But he covers up his anxiety with a nonstop patter of jokes, observations, and affirmations. I really like Strassner in this film – he’s a big, quick-witted guy in the mold of an early Jack Black, and you get a sense that Cliff was once a big dog on the local comedy scene. But now he’s like a stray St. Bernard looking for a home, surprisingly gentle and sweet.
Entering his future in-laws’ house for Christmas Eve dinner, Cliff trips and hits his face on the front door, chipping a molar. In agony, he goes searching for a dentist who can help him, and finds Didi (Liz Larsen). Alone on Christmas Eve, her daughter and granddaughter with her no-good ex, Didi doesn’t have anything better to do. So she puts Cliff in the chair.
Their initial meeting is very funny, especially when Cliff gets a hit of novocaine and starts clumsily flirting with Didi. She’s more amused than annoyed, enough so that when Cliff’s car gets towed, she agrees to drive him into the impound lot.
This launches a long, sometimes madcap, sometimes poignant Christmas Eve for the two accidental companions, one that includes a stint on stage at a comedy club, a little crab fishing, and an ill-advised visit to see Didi’s ex. Another movie would generate circumstances that force Cliff and Didi to stay together, but they seem to genuinely like each other and want to hang out.
Larsen plays Didi as a little flintier and more guarded than Cliff, bruised by life, but she breaks into the most dazzling smile at his open-hearted antics. The two leads have terrific chemistry that occasionally edges into the romantic, and it’s a pleasure to roam late-night Baltimore with them, buoyed by Jordan Seigel’s Vince Guaraldi-inspired piano score.
Duplass is an actor (“Transparent”), but is best known for the indie movies he used to make with his brother Mark, like “Cyrus.” They’ve decided to “consciously uncouple” for now, and “The Baltimorons” retains the Duplass Brothers gift for offhand, scruffy character pieces where people unexpectedly connect, but feels less reliant on improvised dialogue.
Are Cliff and Didi going to go on to become a couple, or just friends, or never see each other after Boxing Day? The movie leaves it somewhat unresolved, but it’s entertaining while it lasts. I usually can’t stand to see anything Christmassy until after Thanksgiving, for “The Baltimorons” I’ll make an exception.
“The Baltimorons” is now in theaters. In Madison, it will open Friday at AMC Fitchburg 18.


This sounds like fun, and I'll see anything Duplass. Thanks, Rob!